Diethylstilbestrol

Synonym(s):(E)-3,4-Bis(4-hydroxyphenyl)-3-hexene;DES;Desmin;Stilbestrol

CAS NO.：56-53-1
Empirical Formula: C18H20O2
Molecular Weight: 268.35
MDL number: MFCD00002373
EINECS: 200-278-5
SAFETY DATA SHEET (SDS)
Update Date: 2024-03-26 17:16:27

What is Diethylstilbestrol?

Toxicity

Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.

Description

Diethylstilbestrol (DES) is a synthetic estrogen receptor agonist that was prescribed to pregnant women in the late 1930s. It was banned in 1971 because of possible links to increased risk of breast cancer in mothers along with congenital abnormalities and increased risk of cancer in offspring. DES is structurally related to, and is as potent as, estradiol in most assays, with a longer half-life. It has a relative binding affinity to sex hormone binding globulin (SHBG) of 0.2 compared to estradiol which has a relative binding affinity of 100. A concentration of 20 μM DES, displaces 30 ± 13% of 3H-estradiol from SHBG in serum.

The Uses of Diethylstilbestrol

Diethylstilbestrol is a synthetic nonsteroidal estrogen that was formerly used in estrogenic hormone therapy (for menstrual disorders, postpartum breast engorgement, postcoital contraceptive, prevention of spontaneous abortion) and in chemotherapy of various cancers, including postmenopausal breast cancer and prostate cancer. It was also used in biomedical research and veterinary medicine (growth promoter for cattle and sheep; veterinary drug to treat estrogen deficiency disorders).

Background

A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed)
The FDA withdrew its approval for the use of all oral and parenteral drug products containing 25 milligrams or more of diethylstilbestrol per unit dose.

Indications

Used in the treatment of prostate cancer. Previously used in the prevention of miscarriage or premature delivery in pregnant women prone to miscarriage or premature delivery.

What are the applications of Application

Diethylstilbestrol is a synthetic estrogen

Pharmacokinetics

Diethylstilbestrol is a synthetic estrogen that was developed to supplement a woman's natural estrogen production. In 1971, the Food and Drug Administration (FDA) issued a Drug Bulletin advising physicians to stop prescribing DES to pregnant women because it was linked to a rare vaginal cancer in female offspring.

Metabolism

Hepatic.

Properties of Diethylstilbestrol

Melting point:	170-172 °C(lit.)
Boiling point:	351.51°C (rough estimate)
Density	1.1096 (rough estimate)
storage temp.	2-8°C
solubility	methanol: 0.1 g/mL, clear, faintly yellow
form	Crystalline Powder
color	White to almost white
Water Solubility	PRACTICALLY INSOLUBLE

Safety information for Diethylstilbestrol

Signal word	Danger
Pictogram(s)	Exclamation Mark Irritant GHS07 Health Hazard GHS08 Environment GHS09
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation H350:Carcinogenicity H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P202:Do not handle until all safety precautions have been read and understood. P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P273:Avoid release to the environment. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P308+P313:IF exposed or concerned: Get medical advice/attention.